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I have this thing I want to do with a playlist on my iPhone so that it sounds like a radio station I grew up listening to in the 60's. I have all the airchecks I need from CKLW Windsor and the Big 8 Jocks, and I need to figure out how to get them in there every two or three songs so they don't clump together and play one after another, which would sound pretty weird and ruin the effect.
All I can think of is to edit the airchecks into the start or end of certain songs, or number everything on the list and turn off shuffle...